At some point, we are going to run into challenges in our workplace. Whether it’s about a project we’re working on or clashes with a co-worker, and our efforts toward a solution have not been successful, it’s inevitable not every day is going to be smooth.

Sometimes we realize that we need more assistance and the help has to come from our boss or manager. Your boss’s personality type might also add to the challenge of approaching him or her with your concerns. Your boss’s time is likely limited, just as your time is.

What are the best methods for communicating challenges? How can you make sure you walk away from the discussion with satisfying answers? Is there a way to keep the dialogue positive and strengthen your boss’s view of your value?

Plan ahead

Take some time to catalog and write down your challenge(s) so it is clear to you. What is the situation? What led up to the issue? Have you done the necessary research to understand the circumstances? You want to be sure that you are clear on the matter, you’ve done all you could reasonably do up to a point, and that you recognize you need further guidance or assistance.

Also, make sure you understand your manager’s personality and the best way to approach him/her. Is he a straight-forward, stick to the facts kind of person? Does he need time to absorb the conversation before you have a response? Or do you need to focus on feelings and how the decision could affect fellow employees?

Know when there is an appropriate time or if you need to schedule a few minutes. When you’re ready to approach your supervisor, you want to have a solid response when you ask for his/her time. “I would like 15 minutes of your time this week to discuss (this project). When would be a good time?”

Outline questions

Write down questions you’d like to ask your supervisor in a way he/she realizes you’ve done your homework. Sometimes, your supervisor may not have enough background to know how to respond. Avoid framing your questions in a way that might make your manager sound clueless. But do make sure you give him/her the information he needs to grasp the concept of what you’re trying to work out.

The way you shape your questions is important because you want your boss to feel you are tapping into his expertise:

“Is this an issue others have run into?”
“How has this been successfully handled in the past?”
“What would you say I’m overlooking?”

Focus on the positive

Avoid launching into a negative tirade from the outset. While it’s true you might have been granted only a few minutes with your supervisor, you want to approach the brief conversation with a positive attitude. You need to have the mind-set that your goal is to realize a solution and that you’re open to ideas to make the situation work.

Have the mind-set that your goal is to realize a solution

If you begin by stating the problem, that sets up the meeting with negative thinking.

Instead, begin by conveying your appreciation for the opportunity you’ve been given with the task. Or, if your conversation has to do with another employee, you could point out this employee’s positive qualities or something you appreciated about a task he performed.

Briefly express the positive aspects of the current situation you’re dealing with and what you’ve learned from it.

For example: “First, I want to thank you for assigning me the XYZ project. In the last few weeks, I’ve learned a lot from my research, such as (A,B,C). And I appreciate that you have confidence in my abilities to execute this assignment.”

Communicate challenges clearly

After you’ve expressed a few positive aspects and you’ve made sure your supervisor has all the background information, explain the challenges you are facing.

This is where your research and clear understanding will be important. You want to make sure you show your manager that you have researched all the avenues available to you. Part of your challenge might be that you don’t understand all aspects of the situation, so do make it clear everything you understand.

Show your manager that you have researched all the avenues available to you

In your planning process for this conversation, it is best to review all your facts and even have a “practice” conversation in front of a mirror so you have a good idea of what you want to say and how your body language is transmitting your speech. This will also help you make sure you have outlined the appropriate questions and concerns.

When expressing your challenges, it would essentially be in this order:

This is the challenge
This is the research I’ve studied
This is what I’ve tried
This is the result

Your goal here is to show your supervisor your capabilities, but that you recognize your current limitations.

Offer solutions

This is a challenge in itself since the reason you are approaching your boss is because you seek solutions.

What this means is: separate from what you’ve already tried, your research revealed certain possibilities. Or perhaps others on your team made particular suggestions, but before you wished to take it further (perhaps because of cost constraints), you wanted your supervisor’s wisdom in the matter.

When you outline the proposed solutions, also outline the pros and cons to each. Again, this shows you have given considerable thought to the ideas.

Sometime between “communicating challenges” and “offering solutions,” you want to have visual aides to highlight all the aspects of the challenge if it’s a project (not necessarily with a problem co-worker). Whether this is a financial outline, graphics, or a model of the design, your information will resonate deeper with these aides.

This will strengthen your value with your supervisor because he/she sees that you have done all your homework and you are determined to realize a productive solution.

Ask for advice

At the end of the meeting, you are going to get to your point: ask for advice.

Here is where your questions you outlined come into play. Throughout the conversation, your supervisor might have offered ideas and pointed out areas you may have overlooked. Keep an open mind, even if you might disagree with the advice. Remember, you approached your boss for his help, so allow him to give it to you.

Write down the suggestions and understand how he wants you to approach them. What other areas do you need to explore to be clear on how to handle the matter? If you are not sure of what he wants you to do, ask follow up questions.

Thank your boss

At the end of the conversation, be sure to thank your boss for his time and his advice. Thank him for allowing you to express your concerns. Explain to him what your next step will be and how quickly you will implement his suggestions. You might even express something he said that resonated with you and/or something you learned from that conversation.

Managers need to feel appreciated too. By keeping the conversation positive and by ending it on an encouraging note, you leave the door open for future, non-combative conversations.

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